The Most Powerful First Daughter of All Time Was Not Ivanka Trump

Move over Ivanka: Anna Roosevelt Dall, FDR’s oldest child and only daughter, wielded her Washington magic long before the Trump era. She's seen here at a 1935 gala, chatting with Raymond T. Baker, former director of the U.S. Mint.

It was the meeting of the century, three giants of history divvying up the postwar world order. As a result, President Franklin Delano Roosevelt’s traveling party was rather exclusive in 1945 when he journeyed to Yalta to gather with the Soviet Union’s Joseph Stalin and Great Britain’s Winston Churchill. At Roosevelt’s side on the critical voyage was not his famous wife, Eleanor, but his daughter and confidante, Anna Roosevelt Boettiger — the most powerful adviser in the White House at the close of FDR’s massively consequential presidency.

“I wanted desperately to go, you see,” Anna later wrote to a friend. “But I also knew if mother went I couldn’t go.” That Anna won out over Eleanor was a sign both of the Roosevelts’ rocky marriage and the power the first daughter had amassed by supporting her father’s gregarious side. In her father’s last year as president, Anna “was practically running it, holding it together,” says Doug Wead, author of All the Presidents’ Children: Triumph and Tragedy in the Lives of America’s First Families.

[Ivanka will] endure in her relationship and her access with her father.

Doug Wead, author, All the Presidents’ Children

The current White House called Ivanka Trump’s elevation as a top adviser “unprecedented,” and her West Wing office is a new wrinkle. But adult children of presidents have long enjoyed heavy influence. John Quincy Adams hired his son as a personal secretary; John Eisenhower was a White House adviser to father Dwight on national security matters; and George W. Bush played a critical role in his father’s campaigns, though he did not officially join the government.

Presidents place high value on loyalty, which can work to undermine them. Wead, who worked in George H.W. Bush’s administration and wrote a book, Game of Thorns, about the 2016 campaign, says decision-making paralysis can set in among White House aides who want to dodge blame. A presidential progeny who cannot be fired, however, is freer to make tough calls. “She’ll endure in her relationship and her access with her father,” Wead says of Ivanka.

President Trump, Ivanka Trump and Canadian Prime Minister Justin Trudeau (right) at a February roundtable discussion on the advancement of women entrepreneurs and business leaders.

By contrast, Anna’s role blossomed late in her father’s 12-year presidency. The eldest child and only daughter, she was known as “Sis.” Her second husband, John Boettiger, was a newspaper publisher — as Ivanka’s husband, Jared Kushner, was — and Anna was an editor and columnist for the Seattle Post-Intelligencer for several years. But in 1943 she left Seattle for Washington as FDR’s unofficial secretary, and her husband joined the military. Anna set up shop in Pennsylvania Avenue to handle correspondence and write speeches; while not physically located in the West Wing and mostly out of the public eye, she increasingly wielded power. In personality, she was closer to her father than to the introverted Eleanor; Life magazine referred to her as the “free-speaking, free-cursing” daughter. This gave her access to and influence over FDR that came to eclipse that of his wife, as he found in Anna a sympathetic and trustworthy ear. According to Doris Kearns Goodwin in No Ordinary Time: Franklin & Eleanor Roosevelt: The Home Front in World War II, “[t]hough he rarely chose to reveal to anyone the full extent of what he was thinking or feeling, he spoke openly to Anna about his frustrations with Eleanor.”

While Eleanor traveled the country more and more to investigate poverty and civil rights — encouraged by FDR to be his “eyes and ears” — Anna became the first lady de facto. At varying times she played hostess, drinking partner and gatekeeper. Anna helped plan the 1944 presidential campaign and became a critical player as World War II raged on. By that point, Roosevelt’s right-hand man, Harry Hopkins, was often sick and absent. But Anna’s rise came at Eleanor’s expense. At one point, the first lady handed the president a stack of papers for his perusal. He immediately passed them to Anna, saying, “Sis, you handle these.” Anna later recalled the incident in a letter, acknowledging “embarrassment” at the hurt her mother must have felt. It had been a slow progression, according to an account in Lifein March 1945. “She took to having lunch with him, just to make sure that he laughed and ate his food,” the report said. “And pretty soon she found herself doing other things.”

Anna Roosevelt and her second husband, newspaper publisher John Boettiger.

Anna indulged FDR but also tried to make sure he got rest as the president’s “ticker trouble” — as she called it in letters — worsened. The president died just two months after Yalta, on April 12, 1945, during a visit to Warm Springs, Georgia. His mistress, Lucy Mercer Rutherfurd, was there, but his wife was not, and Eleanor was hurt that Anna had concealed her father’s extramarital liaisons. But mother and daughter later reconciled and hosted a radio show together, The Eleanor and Anna Roosevelt Program, which gave the real former first lady top billing.